


Pretty Good Bad Idea

by musicaldork



Category: Critical Role (Web Series), Waitress (2007), Waitress - Bareilles/Nelson
Genre: Bad Decisions, F/M, Fluff, Fluff and Smut, Gentle Kissing, Gentle Sex, Gentleness, Making Love, Oral Sex, Plot What Plot/Porn Without Plot, Porn, Porn with Feelings, Resolved Sexual Tension, Romance, Sex, Sexual Content, Smut, Sweet, Vaginal Fingering, Vaginal Sex, technically there is plot if you check out the fic it belongs to ;)
Language: English
Status: Completed
Published: 2020-04-24
Updated: 2020-04-24
Packaged: 2021-03-02 02:20:49
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,460
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23827504
Author URL: https://archiveofourown.org/users/musicaldork/pseuds/musicaldork
Summary: The company that Caleb keeps is severely limited to the books he pores over.Jester's life is a complete and utter shitshow.Finding themselves in each other's orbits, they've finally crashed together in the culmination of everything they want and everything they need.They make each other feel loving and deserving and good - things they thought they'd both lost a long time ago.And sometimes, bad decisions need making.(An NSFW elaboration on Chapter 11 of my fanfic 'Words of a Sugar-Sweet Waitress'!)
Relationships: Jester Lavorre & Caleb Widogast, Jester Lavorre/Caleb Widogast
Comments: 6
Kudos: 49





	Pretty Good Bad Idea

Caleb thinks himself a very bad man.

He knows it in the same way that he knows the sky is blue, or that grass is green. That he is not good.

And although he knows he is not good, in this particular moment, he can't find it in himself to care.  
Not when he's on top of a gorgeous, blue tiefling, who's looking up at him like he hangs the stars in the sky.

His heart - the traitorous muscle it is - skips another beat at the feeling of her eyes on him.

He wonders what she sees.

Caleb notices - not for the first time, mind you - the curve of her lips, the constellation of freckles on her cheeks, and the scrunch of her nose when she smiles that ever-beaming smile that feels like redemption in its purest form. It makes him feel like he could be good. Like he wants to be good for her.

What dangerous thoughts for a man like him to have.

Putting his thoughts aside, an unhurried, magnetic pull draws them together this time, and when they meet, it’s not like fireworks. It’s like coming home. There's a slow culmination of unprecedented familiarity between the two of them that makes them burn hot with careful need. 

The strength of their need to seek solace in one another seizes them feverishly, and adamantly refuses to let go.

He feels her start to smile into the kiss, and they break apart with breathless, giddy laughs before meeting again.

He could do this forever and consider it his own little slice of the heaven he doesn’t deserve.

The last remaining shreds of Caleb's resolve buckle and collapse from under him as she pulls him eagerly in for a deeper, more heated kiss, her tail twining impishly around his thigh.

Leaning his body into hers, he makes sure not to go any further than that for now. If he pushed further than she was comfortable with, he'd truly never forgive himself. Never mind the fact that this shouldn't be happening at all. What matters to him right now was only her.

"I don't... I mean, I know I'm nothing special, but if you'd like... you can touch me, you know?"

Almost shyly, she leads his hand up to the soft swell of her breast and it's with a sudden jolt that he realises just how incredibly turned on he is. It burns up fiercely bright inside of him and sets him alight.

And then a second later he registers her words, and he stirs with the heat of an anger long forgotten at the thought - even the most infinitesimal implication - that this wonderful woman could be considered anything other than utterly breathtaking - to anybody at all.

Somebody has made her feel less than, and he finds the thought of that completely unacceptable.

It is with breathless desire that he realises that he wants to kiss every last piece of that doubt away from her.

"You’re more than special, Jester. You are incredible, you are unearthly and you are so, so beautiful. It is everyone else who is undeserving of you and your light."

"Oh."

Jester goes to tuck her face into the pale hollow of his neck to hide in reflexive shame, but softly, he moves back and meets her gaze.

There aren't any words exchanged, but as he stares into the depths of her wide, violet eyes, he thinks he understands her a little better.

Bringing a gentle hand up to cup her cheek, he treats her like he’s offering her the most reverent worship. He may as well be, with the way his senses are overwhelmed by her. He watches as she turns and nuzzles sweetly into his palm. 

Her long, dark eyelashes flutter against her cheeks; she looks bewildered, as though a gentle touch is foreign to her **.** Caleb's heart squeezes at the thought. He wants to change that.

But oh, she's so soft against him - like a goddess among men. It's one of the many distracted notes his brain takes for him of the situation at hand.

Caleb's never been a religious man, but 'goddess', 'angel', and 'radiant light' are the only words that come to mind as his gaze lingers over her body - blue skirts hitched up just high enough on her thighs that it makes his mouth go dry at the sight. If this is what divinity looks like, he thinks he could be persuaded to believe in her.

“Jester?" he says, for the first time trying out her first name on his tongue. He finds that he quite likes the feel of it. And from her pleased shiver, it seems like she does too.  
She hums her acknowledgement, face still tucked away into his neck.

"Yes, Widogast?"

"Please… call me Caleb."

"Okay, what is it, _Cayyyleb_?"

And now he knows how she must’ve felt. The honeyed drag of his name from her softly parted lips sends him reeling, sending another steady pulse of arousal thrumming through his blood.

"I… I want to see you. Is it okay if I see your face?”

Jester lets herself bask in the lingering kisses he leaves on her lips, on her neck, on her face, and all over, then nods wordlessly. This feels right.

She leans back and the feel of his eyes on her sends a thrilled buzz through her body. She doesn't feel sized up. With him, she feels _seen_. And what a delectable feeling it is.

There are so many things Jester is thinking right now.  
‘ _This shouldn’t be happening. This is a bad idea. I’m making a mistake.’_

But all rational thought is dulled between them like they've been lost within the sleepy haze of a long-forgotten dream, completely insignificant to the feel of their bodies against each other.

This is a mistake, but she thinks that it might be the best one she's ever made.

And after everything… doesn’t she deserve to **_feel_** for once in her life?

With rapt attention, he notices that for a moment she seems rather absent, as though lost in her own thoughts.

"...Are you alright, Jester? We can stop if you need to-"

"I want you."

Caleb pauses at the bluntness of her words and swallows tightly against the knot in his throat.

He wishes for the gods to grant him clemency for this sweet, irresistible sin of his, and then nods, and lets his hands explore every inch of her body.

He watches the stark contrast his pale hands make against the soft, blue curves of her skin and he thinks that there's never been a luckier man in the world than he. He wants to map out her body and never forget it. 

He wants to touch and kiss every freckle, every stretch mark, and every single inch of the plush softness of Jester and tattoo it onto the inside of his brain. He doesn't have the time for it, but he tries his best.

As much as he doesn't want to, he pulls away from her for a moment.

Caleb starts to pull off his long white coat, but his arms catch inside the sleeves in his eagerness to disrobe, and he struggles awkwardly.

He hears Jester giggle, but it’s a warm, lovely sound, and he doesn’t seem to mind it at all. He just flashes her a shy grin, finally shedding it, before playfully pulling her into him by the hips.

Oh, gods, it should be illegal how good he looks right now, Jester can't help but think. With wrinkled, half-unbuttoned dress shirt, and kiss-bruised lips, he looks like a beautiful mess

Moving slowly as if giving her a chance to stop him if he needs, he grows a little bolder with his touch.

She feels his hand reach between her soft, blue thighs and find something _wonderful_.

He works his hands against her, inside her, attentively - almost as sweetly as the man himself. She’s so slick and _hot_ around him, it makes him dizzy. He could get addicted to the feel of having his fingers inside her, and the pure electricity he feels from being on top of her.  
His movements are gentle, but not teasing and Caleb finds that he can’t tear his eyes away from her face.  
Jester, feeling the intensity of his gaze on her, avoids the temptation to tuck her face away and lets him see her.

With soft, desperate exhales puffing against his heated skin, an uncontrollable moan tears itself out of her body as it sings its pleasure in response to him.

She lets out a _whine_ , and flushes all over with unbidden embarrassment. Wordlessly, he begins to ease it with the gentle, circular motions of his calloused thumb against her hip. It's surprisingly chaste in its tenderness, and it's exactly what she needs.

“It’s… it’s okay. You sound so, so beautiful, liebling. Uh-”  
She can tell that he’s going to go on another rambling tangent. And as cute as she finds it, she doesn’t need it right now. 

“Caleb? Shh. Just kiss me, okay?”

He swallows hard at the beautiful appeal in her words, and _scheisse_ , how could he not acquiesce to a suggestion like that?

She could probably ask him to leap off a cliff right now, in that sweetly demanding tone of hers, and he'd only ask if she wanted a running start from him.

Suddenly summoning up every last reserve of his courage to ask, Caleb raises a question that Jester honestly isn't expecting at all.

"Do you want me to _taste_ you… _here?”_

He punctuates his last word with a firm, deliberate touch to the apex of her thigh, before resting his hand there. **  
**Caught off guard by the question, Jester's _very intelligent_ answer to this is a bewildered ‘huh?’

She can't remember if she's ever had good oral. The men she'd been with rarely, if ever, wanted to pleasure her with their tongues. Then of course, they'd expect a blowjob in return for nothing, she thought, with a barely-suppressed eye roll at the deluge of disappointing memories.  
But everything about the way he treats her is so attentive...  
She really wants to give it a shot.

"Most people haven’t… but yes, I’d love that."

With unexpected heat in his voice that deepens his words into almost a growl, and a palpable, honest hunger in his eyes, her need for him becomes near unbearable in its sudden flare of intensity. She wants him so badly.

Caleb briefly wonders how anybody could possibly avoid jumping at the chance to find out all the things about her that make her tick. How they could resist the desire to make her come apart for them.  
He's having an amazing time of it himself, so far. He wants to so badly.

Caleb has a set to his jaw that makes him look like a man on a mission; the mission with his name written on it is his one concrete goal of pleasuring her until her mind goes blank.

"Well, if you'd allow it, I'd like nothing more than to taste you, and see you come apart on my tongue."

He sounds more sure of himself than she's ever heard him and fuck, it's hot. Before she’s even aware of it, she's sighing out his name in breathless agreement.

"Yes, Caleb, please..."

Next thing she knows, she's been gently guided to sit at the edge of the table. He's kneeling before her, pulling her underwear off (she curses the fact that she didn't wear a nice pair, but how did she know she'd end up here?) and then his face is pressed eagerly between her thighs.

The gentle scrape of stubble against Jester's inner thighs is something that feels so good, she doesn't know how she's ever lived without it.  
Her heart whispers to her that she likes him for more than what he does to her, but she shuts it off. Not the time.

Their eyes meet. That's the only warning she gets before she feels his lips and his tongue pressing into her. 

He eats her out like a man starved, greedily pulling her into him by the hips. The feel of his rough fingers sinking into her skin makes her shiver.  
Caleb takes it upon himself to wedge himself so firmly against her that his nose sinks into her dark curls. She can’t stop herself from grinding against the eager warmth of his tongue, and he seems more than happy to give her whatever it is she wants to take from him.

What she's gotten used to in her past experiences were all sloppy and disappointing. This is anything but. It's so good she doesn't know what to do with herself. She gasps - a noise breathy and high with pleasure - and her hand immediately shoots down to grip the back of his hair - _hard_. 

She's about to apologise before she feels the vibrations of his low, pleased groan against her, and oh Traveller it feels _amazing_. It sounds like he liked that.  
(A hair-pulling kink? Shamefully, she files the thought away for later, when she's feeling lonely.)

He looks absolutely amazing and _god_ , she'd die with him in between her thighs if she could.

What's miraculous, is that when she tells him what she likes and what she doesn't, he _actually listens_.

It's rare enough of a quality she finds it ridiculous how appealing it is to her. He doesn’t posture and act like he’s the one who knows best, he just adjusts himself accordingly to her reactions.

And he's so focused... when he finds something that makes her twitch and grip his hair tighter, he notices it and keeps going - his tongue soft and pliable against her sensitive bundle of nerves.

It doesn't take long before she knows she's approaching her end, faster than she's ever felt an orgasm come on. But she's not in the mood to stave it off to save her pride. With a gentle sweep over her clit, it’s the last push she needs to reach that peak of overwhelming pleasure-

Caleb feels her thighs clamp around his head tightly as she comes. And the sounds she makes, oh god, they're too much for him. He could get off on the noises she makes for him alone. 

She makes him feel like a hormone-addled teenager, but he knows it's more than that. But that's too much to think about for the time being. So instead, he busies himself by working her through her climax with gentle kisses and touches, letting her regain her bearings.

"Would you like to keep going?" he asks her, careful not to push.

Despite the fact that he's desperately hard, she can tell that it’s the farthest thing from a demand. He's the very definition of a gentleman and it makes her want him more.  
The onus is on her. She likes him so much. Desire for him still courses through her veins, and she wants nothing more than to touch him but... is she really going to take this further?

One more look at the wrecked, flushed look on his face gives her her answer.

_Absolutely._

"...Caleb, I really want you inside of me."

And although a searing blush rises to his cheeks at the words, he gives her a patient nod and moves slowly, though god knows the poor man must be as taut as a bowstring at this point.

Half-a-minute later Jester coaxes him forward with a small, lopsided grin. He finds that it clutches at his heart and refuses to let go. 

At her signal, Caleb crawls on top of her, carefully propping himself up above her - remaining mindful not to drop all of his weight on her. He knows that she’s not delicate but he finds that he wants to treat her with every last ounce of tenderness he has within him.  
Caleb feels as though she deserves nothing less.

With little fanfare, they finally join together in a slow, blessed slide, his hips pushing forward.  
Happy sighs and soft pants of breath accompany that incredible feeling of finally being together. Shakily, he presses tender kisses to her shoulders and laves his tongue over every exposed patch of skin, mostly to distract himself from just how amazingly hot and slick she feels around him.  
His hands are all over her now, and she returns the favour with soft, small hands and curiosity-fuelled fervour.

He feels so good inside her, and she's so wet...

From there, it doesn't take long for them to start rocking their hips together, shallowly at first, before the pace picks up in mutual desperation for each other. His thrusts are slower, but deliciously deliberate in a way that makes her clench tightly around him.

Jester suddenly reaches between them and starts to touch herself, openly relishing in the feeling of him inside her.  
He admits that his jaw drops a little at the sight. She’s just breathtaking.

She sees him look up at her like she’s a thing of beauty and she can’t make sense of it.  
He looks at her... like she's something worth looking at.

The heat in his darkened, blown-out pupils - and the desire-drunk expression that goes hand-in-hand with it - absolutely floors her. Nobody’s looked at her like THAT.

With respect and care and desire, and everything else in between. It's really nice to be looked at like 

Distantly, she thinks that she could get used to this. And she finds the thought incredibly dangerous.

His movements grow clumsier - but no less adoring - as he nears his end. She basks in the feel of him on top of her, but unexpectedly she finds his hand reaching for hers, and fumbling until his fingers lace with hers. She squeezes the hand tight, and he squeezes back.

It's intoxicating to feel alive, and to know that they're here in this moment, _together_.

With her hand working at her clit, the wet kiss he presses to the hollow of her throat is the last push she needs before she comes undone.

The look of uncontrollable bliss on her face, the feel of her fingers intertwined with his, the way she makes the sexiest noises he's ever heard in his damn life... It's all too much for him. His hips stutter, and he pulls out, painting the flesh of her inner thighs in white. Somehow, for a moment it feels like everything is going to be okay.

They breathe together and come down from it together, hearts slowing to beat steadily in sync.

When Jester finally finds the strength to tear herself away from him, they both get up off the examination table. She feels the wetness between her thighs and flushes, but she can't say that she's completely turned off by the reminder of him inside her.

And they both know that it's terrible, it's horrible, what they just did. Regardless, they collapse into breathless, nigh-hysterical giddy laughter at finally finding reprieve from the sexual tension between them. It feels ridiculous, and the implications haven't set in yet, but they're not at all unhappy.

As the afterglow begins to fade, the two of them take on the task of helping each other neaten themselves up.  
Jester’s thankful for the support as her knees wobble from underneath her.

Caleb’s attentive hands pull the bunching fabric of her skirt back down over her upper thighs and carefully begin to smooth down her untidily tousled blue bob.

Jester allows herself to fiddle with the buttons of his dress shirt, adjusting an askew collar here, running her hands through an unruly red curl there. 

They’re so close to each other that she can feel the heat radiating from his body.

If either of them note that their shared touches linger and remain on the skin a little longer than necessary, they don’t mention it.

The spell of silence is broken with a broken stutter from Caleb’s lips.

“Ah, I’m sorry for making a mess!” 

He juggles with an embarrassed, frantic apology as soon as he sees the evidence of their time together begin slide down her thigh.  
His pale face is overcome with a startling red as he hands her a couple tissues to clean herself up with, eyes averted deliberately. 

Jester finds it way too adorable that after all that, he’s still just as sweetly awkward as he’s always been.

Before she can think to stop herself, Jester reaches over to give his hand a quick, reassuring squeeze. The moment hovers and then passes.  
She leaves the clinic wordlessly, but there's a skip in her step that wasn't there this morning when she starts the long journey to work.

And although she knows she shouldn't be, Jester finds herself very pleased with the mistake she’s made.

**Author's Note:**

> Much love to my two beta-readers for this fic: songsforfelurian and PetiteWolverine!


End file.
